Synthesis and characterization of 3,6-bis(1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz): Novel high-nitrogen content insensitive high energy material

Saikia, Anil K.; Sivabalan, R.; Polke, B. G.; Gore, G. M.; Singh, Amritpal; Rao, A. Subhananda; Sikder, A. K.

doi:10.1016/j.jhazmat.2009.04.095

Cited by 56 publications

(31 citation statements)

References 19 publications

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“…1,2,4,5-tetrazine, as one of the promising nitrogen rich [6][7][8][9][10][11][12] EMs, has a nitrogen content of 68.3% in the six-member ring, which makes them present high density and easily obtain oxygen balance, furthermore, the main combustion product is clean gas N 2 [13]. Therefore, they are considered as green energetic materials used in solid propellants, explosives, and civil combustible gas generators [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and thermodynamic properties of 3-(3,5-dimethylpyrazol-1-yl)-6-(benzylmethylene) hydrazone-s-tetrazine

Yao

Chen

et al. 2017

The Journal of Chemical Thermodynamics

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Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and thermodynamic properties of 3-(3,5-dimethylpyrazol-1-yl)-6-(benzylmethylene) hydrazone-s-tetrazine

Yao

Chen

et al. 2017

The Journal of Chemical Thermodynamics

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“…To our best knowledge, recent investigations of 1,2,4,5-tetrazine derivatives have mainly focusedo ni ntroducing energetic groupst ot he carbon atoms by nucleophilic substitution reactions. [6][7][8] This is because the stronge lectrophilic effects of the nitrogen atoms reduce the electron density that is distributed on the carbon atoms, and then thesec arbon atoms easily attractn ucleophilic reagentst of orm various 1,2,4,5-tetrazine-based energetic derivatives. However,e ach of these compounds has different advantages and disadvantages with respect to its stabilities and detonation properties.…”

Section: Introductionmentioning

confidence: 99%

Exploration of High‐Energy‐Density Materials: Computational Insight into Energetic Derivatives Based on 1,2,4,5‐Tetrahydro‐1,2,4,5‐tetrazine

Jin

Zhou

2018

ChemistryOpen

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Density functional theory was employed to investigate ten 1,2,4,5‐tetrahydro‐1,2,4,5‐tetrazine‐based energetic materials. The heats of formation and detonation properties were calculated by isodesmic reactions and Kamlet–Jacobs equations. The thermal stabilities and impact sensitivities were also estimated to give a better understanding of their decomposition mechanism. The results indicate that all of the designed compounds have high positive heats of formation ranging from 525.1 to 1639.1 kJ mol−1, moderate detonation properties (heats of detonation of 536.6 to 2187.6 cal g−1, theoretical densities of 1.48 to 2.32 g cm−3, detonation velocities of 7.02 to 12.18 km s−1, and detonation pressures of 19.8 to 75.1 GPa), and acceptable stabilities (bond dissociation energies of 0.8 to 104.9 kJ mol−1). Taking both the detonation properties and the stabilities into consideration, compounds A4 and B4 were finally selected as promising candidates of high‐energy‐density materials, as their detonation properties and impact sensitivities were superior to those of HMX. Additionally, the frontier molecular orbitals, electronic densities, electrostatic potentials, and thermal dynamic parameters of compounds A4 and B4 were also investigated.

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“…1 H NMR (400 MHz, DMSO-d 6 ): δ 8.65 (s), 11.35 (br s). 13 N 3 ,N 6 -bis(3-nitro-1H-1,2,4-triazol-5-yl)-1,2,4,5-tetrazine-3,6diamine (20). HNO 3 (99%; 2.5 mL, 60.02 mmol) was added to acetic anhydride (7.5 mL, 79.49 mmol) at 0 °C and the mixture was stirred for 30 min.…”

Section: General Informationmentioning

confidence: 99%

The nitration pattern of energetic 3,6-diamino-1,2,4,5-tetrazine derivatives containing azole functional groups

et al. 2015

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One of the successful strategies for the design of promising new energetic materials is the incorporation of both fuel and oxidizer moieties into the same molecule. Therefore, during recent years, synthesis of various nitro-azole derivatives, as compounds with a more balanced oxygen content, has become very popular. In the framework of this effort, we studied nitration of N(3),N(6)-bis(1H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine (BTATz; ) and its alkylated derivative N(3),N(6)-bis(2-methyl-2H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine , using a (15)N-labeled nitration agent and monitoring and analyzing products of these reactions by (15)N NMR. It was seen that the nitration of both compounds takes place only on the exocyclic ("bridging") secondary amine groups. Possible tetranitro derivative isomers N,N'-(1,2,4,5-tetrazine-3,6-diyl)bis(N-(1-nitro-1H-tetrazol-5-yl)-nitramide) and N,N'-(1,2,4,5-tetrazine-3,6-diyl)bis(N-(2-nitro-2H-tetrazol-5-yl)nitramide) , both of which have OB = 0% and calculated VODs of 9790 and 9903 m s(-1), respectively, could not be observed in the reaction mixtures, during the in situ(15)N NMR monitoring of nitration of , using (15)N-labeled nitrating agents. Following a similar strategy, a new analog of BTATz - N(3),N(6)-Bis(1H-1,2,4-triazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine was obtained and its nitration was studied. The reaction of with a HNO3-Ac2O nitration mixture resulted in the formation of a new N(3),N(6)-bis(3-nitro-1H-1,2,4-triazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine derivative in a moderate yield. Structures and properties of (in the form of its perchlorate salt, ) and were measured by FTIR, multinuclear NMR, MS, DSC and X-ray crystallography. It is important to note that compound exhibits exothermic decomposition at 302 °C (DSC) and >353 N (sensitivity to friction), making it a highly-promising thermally-insensitive energetic material for further development.

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Synthesis and characterization of 3,6-bis(1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz): Novel high-nitrogen content insensitive high energy material

Cited by 56 publications

References 19 publications

Synthesis, crystal structure and thermodynamic properties of 3-(3,5-dimethylpyrazol-1-yl)-6-(benzylmethylene) hydrazone-s-tetrazine

Synthesis, crystal structure and thermodynamic properties of 3-(3,5-dimethylpyrazol-1-yl)-6-(benzylmethylene) hydrazone-s-tetrazine

Exploration of High‐Energy‐Density Materials: Computational Insight into Energetic Derivatives Based on 1,2,4,5‐Tetrahydro‐1,2,4,5‐tetrazine

The nitration pattern of energetic 3,6-diamino-1,2,4,5-tetrazine derivatives containing azole functional groups

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